Stadium: Stadium Round: 27 Ground: Hardcourt outdoor
| ATP Delray Beach | 2018/02/21 20:25 | Steve Johnson v Milos Raonic | 6-2,6-4 |
| ATP Cincinnati | 2014/08/14 18:55 | Milos Raonic v Steve Johnson | 6-7,6-3,7-6 |
| ATP Washington | 2014/08/01 20:00 | Steve Johnson v Milos Raonic | 6-7,2-6 |
| ATP New York | 2020/02/12 18:35 | Andreas Seppi v Steve Johnson | 7-6,6-3 |
| ATP New York | 2020/02/11 00:30 | Steve Johnson v Tennys Sandgren | 6-7,6-3,7-6 |
| Challenger Newport Beach | 2020/02/01 19:25 | Steve Johnson v Thai-Son Kwiatkowski | 6-3,6-7,1-6 |
| Challenger Newport Beach | 2020/01/31 21:10 | Bradley Klahn v Steve Johnson | 4-6,2-6 |
| Challenger Newport Beach | 2020/01/30 18:00 | Aleksandar Vukic v Steve Johnson | 6-7,7-6,6-7 |
| Challenger Newport Beach | 2020/01/29 22:10 | Roberto Quiroz v Steve Johnson | 3-6,2-6 |
| Australian Open | 2020/01/20 03:05 | Steve Johnson v Roger Federer | 3-6,2-6,2-6 |
| Challenger Bendigo | 2020/01/18 01:40 | Steve Johnson v Stefano Travaglia | 7-6,7-6 |
| ATP New York | 2020/02/13 00:30 | Soonwoo Kwon v Milos Raonic | 7-6,6-7,6-4 |
| Australian Open | 2020/01/28 08:00 | Milos Raonic v Novak Djokovic | 4-6,3-6,6-7 |
| Australian Open | 2020/01/26 02:00 | Milos Raonic v Marin Cilic | 6-4,6-3,7-5 |
| Australian Open | 2020/01/24 08:00 | Stefanos Tsitsipas v Milos Raonic | 5-7,4-6,6-7 |
| Australian Open | 2020/01/22 04:45 | Cristian Garin v Milos Raonic | 3-6,4-6,2-6 |
| Australian Open | 2020/01/21 01:35 | Lorenzo Giustino v Milos Raonic | 2-6,1-6,3-6 |
| Kooyong Classic | 2020/01/14 04:35 | Milos Raonic v Soonwoo Kwon | 6-3,6-2 |
| ATP Doha | 2020/01/08 18:05 | Milos Raonic v Corentin Moutet | 6-7,6-7 |